Junior Billing Specialist

Location: San José, Costa Rica Department: SPSC

Location: 100 % remote Contract: Full-time, Independent Contractor   Posting Jurisdictions: To support US Eastern Time working hours

Our Firm

Sterlington PLLC is a full-service law firm focusing on complex corporate, litigation, executive compensation, and private wealth matters. As a firm, we focus on the economics as well as the legal aspects of our matters.

Among other strengths, Sterlington is the ultimate law firm for founders, senior executives, and UHNWIs as well as their related businesses.

Learn more at: www.sterlingtonlaw.com/

The Opportunity

We’re looking for a Billing Specialist to take ownership of invoicing and billing operations in a fast-paced, client-facing environment. This role sits at the center of revenue operations, working closely with partners, finance, and client teams to ensure invoices are accurate, timely, and aligned with client expectations.

You’ll play a key role in keeping billing clean, reducing friction with clients, and supporting overall cash flow.

What You'll Do

Prepare, review, and issue invoices accurately and on time, including billable hours and client-specific billing arrangements

Work closely with partners and internal stakeholders to validate billing details before sending invoices

Track billing schedules and ensure deadlines are consistently met

Review time entries, expenses, and billing data to ensure accuracy and compliance

Resolve billing queries and disputes by coordinating with internal teams and communicating with clients

Maintain clean and organized billing records and documentation

Support month-end processes by ensuring billing data is complete and up to date

Identify recurring billing issues and suggest practical improvements to processes

Partner with collections and AR to ensure smooth handoff from invoicing to payment

What We're Looking For

2–5 years of experience in billing, accounts receivable, or finance operations

Familiarity with AI-assisted billing tools: comfortable using AI features in accounting or ERP platforms to flag anomalies, automate invoice matching, or surface overdue accounts faster

Open to AI-augmented workflows: willing to adopt AI tools that streamline repetitive tasks like data entry, payment follow-ups, or reconciliation, freeing up time for higher-value problem-solving

Strong attention to detail; you catch errors before they become problems

Comfortable working with different billing structures (hourly, fixed fee, retainers)

Clear communicator, able to follow up, clarify, and resolve issues quickly

Organized and able to manage multiple invoices and deadlines at once

Experience with accounting or billing systems (ERP, legal billing tools, etc.)

Solid Excel skills and confidence working with data

At Sterlington, we believe that world-class talent has no boundaries. We are committed to fostering a diverse and inclusive environment where unique perspectives are valued and every individual has the opportunity to thrive. We encourage all qualified candidates to apply.